Pipemidinsure
Pipemidic Acid
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Grundinformationen
- CAS
51940-44-4- Standard-SMILES
CCn1cc(C(=O)O)c(=O)c2cnc(N3CCNCC3)nc21- InChIKey
JOHZPMXAZQZXHR-UHFFFAOYSA-N- Summenformel
- C14H17N5O3
- Durchschnittliche Molmasse
- 303,32 g/mol
- Monoisotopische Masse
- 303,1331394
Überblick
Pipemidic acid is a pyridopyrimidine that is 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid substituted at position 2 by a piperazin-1-yl group and at position 8 by an ethyl group. A synthetic broad-spectrum antibacterial, it is used for treatment of gastrointestinal, biliary, and urinary infections. It has a role as an antibacterial drug and a DNA synthesis inhibitor. It is a monocarboxylic acid, an amino acid, a pyridopyrimidine, a N-arylpiperazine and a quinolone antibiotic.
Namen und Bezeichner
- Bevorzugter Name
- Pipemidic Acid
- IUPAC
- 8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid
- Lokaler Name
- Pipemidinsure
- Englischer Name
- Pipemidic acid
- Summenformel
- C14H17N5O3
- Molmasse
- 303.32
Namen und Synonyme
pipemidic acid51940-44-4PipedacPipemidAcido pipemidicoAcide pipemidiqueAcidum pipemidicumpipeaciduropimidFiltraxPipemidatePipurin
Weitere Namen anzeigen
palin1489rbrb1489pipramdolcolxyliquePB-1489deblaston
TracturUrostenUrovalNurilPi-coli8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acidMemento 400PIPEMIDIC ACID ANHYDROUS
Datenbank-Bezeichner
- CAS
51940-44-4- PubChem CID
- 4831
- DTXSID
DTXSID3023479- ChEMBL
CHEMBL30116- ChEBI
CHEBI:75250- UNII
- LT12J5HVR8
- EC Number
- 257-530-2
- Nikkaji
- J10.405A
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- -2,1
- Polarare Oberfläche (TPSA)
- 98,7 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 489
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Antibiotics
LogP-2.15
Solubility0.322 mg/mL at 25 °C
Human DrugsPharmaceuticals
Melting Point253 - 255 °C
Physical DescriptionSolid
Collision Cross Section
185.6 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
171 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
172.63 Ų [M+H]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 251 · 251-255℃
- Siedepunkt
- 717 ℃ · 717℃
- Dichte
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H317 (97.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Other Safety InformationIMAP assessments - Pyrido[2,3-d]pyrimidine-6-carboxylic acid, 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)-: Environment tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (97.6%)
Sicherheitsdaten
- wgk
- 2
- hs_code
- 29335990
- RTECS-Nr.
- UV1153800
- risk_code
- 42/43
- Toxizität
- LD50 in mice (mg/kg): 4000 orally; 1000 i.p., 50 i.v. (Ficicchia)
- hazard_code
- Xi
- safety_code
- 22-36/37-45
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Mechanism of ActionPipemidic acid is a quinolone antibacterial, which acts by inhibiting the bacterial DNA gyrase DNA topoisomerase IV.
MeSH Pharmacological Classification
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Substances that inhibit the growth or reproduction of BACTERIA.
Verwendung und Herstellung
UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals
Anwendungen
VerwendenPipemidic acid is a quinolone antibacterial drug that is primarily used to treat gram-negative infections of the urinary tract. It is also an antibiotic and cell selection agent. Unlike nalidixic acid, pipemidic acid has a broader spectrum of antibacterial activity and is effective for treating urinary tract and ENT infections.
Darstellung
synthetischeThe synthesis of pipemidic acid involves a series of steps. First, ethyl 2,4-dichloropyrimidine-5-carboxylate is condensed and cyclized with ethyl β-ethylaminopropionate to yield 2-chloro-5-hydroxy-7,8-dihydro-8-ethylpyridine[2,3-d]pyrimidine-6-carboxylate. This compound is then brominated and subsequently condensed with piperazine. The resulting product is hydrolyzed and neutralized to obtain pipemidic acid.
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